嘌呤核酸高氯酸盐与乙酰丙酮反应的意外产物导致 DNA 分子单链断裂

IF 1.4 4区 化学 Q3 CHEMISTRY, ORGANIC
Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov
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引用次数: 0

摘要

首次研究了嘌呤核酸高氯酸盐与最简单的 1,3-二酮--乙酰丙酮的反应。研究表明,腺嘌呤与乙酰丙酮的反应摩尔比为 1:2,反应过程为双环结构的嘧啶片段打开,以甲酸分子的形式消除一个碳片段,然后再生成 8-(4,6-二甲基嘧啶-2-基)-2,4-二甲基咪唑并[1,5-a]嘧啶。反过来,鸟嘌呤以 1:1 的比例与乙酰丙酮反应,生成 7,9-二甲基-3H-嘧啶-[2,1-b]嘌呤-10-鎓-4-醇。在这种情况下,杂环化的方向与鸟嘌呤与丙二醛在体外和体内形成次要核苷酸碱基 M1G 的反应中观察到的方向不同。合成的化合物能够造成 DNA 大分子的单链断裂。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule

Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule

The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio via opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-a]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3H-pyrimido- [2,1-b]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the in vitro and in vivo formation of the minor nucleotide base M1G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.

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来源期刊
CiteScore
2.90
自引率
13.30%
发文量
98
审稿时长
1 months
期刊介绍: The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemo­ra­tives dedicated to prominent heterocyclic chemists.
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